– In his ring debut, Calaway faced Bruiser Brody, managed by Percy Pringle (Paul Bearer).
– On April 1, 1989, the Master of Pain (Calaway) defeated Jerry “The King” Lawler to capture the USWA (United States Wrestling Associated) Unified World Heavyweight title. Skandor Akbar managed the Master of Pain.
– Calaway, as The Punisher, was awarded the USWA Texas title via forfeit from Eric Embry on October 5, 1989.

– In late 1989, Calaway arrived in WCW as “Mean” Mark Callous.
– When Sid Vicious went down with an injury, Callous took his spot in the Skyscrapers with Dan Spivey.
– Callous pinned Johnny Ace at Capitol Combat on May 19, 1990.
– At Clash of the Champions XI on June 13, 1990, Callous defeated Brian Pillman.
– At the 1990 Survivor Series, Calaway debuted in the WWF as The Undertaker. Brother Love (Bruce Pritchard) briefly became his manager.
– In early 1991, Paul Bearer replaced Brother Love as The Undertaker’s manager.
– The Undertaker dominated Jimmy “Superfly” Snuka at Wrestlemania VII.
– The Undertaker defeated Hulk Hogan on November 27, 1991 at the Survivor Series in Detroit, MI to capture the WWF title.
– The Undertaker defeated Jake “The Snake” Roberts at Wrestlemania VIII.
– At Summerslam ’93, The Undertaker defeated Giant Gonzales in a “rest in peace” match.
– Lex Luger, the Steiner Brothers, and The Undertaker defeated Quebec Jacques, Yokozuna, Crush, and Ludvig Borga at the 1993 Survivor Series.
– At Summerslam ’94, Paul Bearer’s Undertaker defeated Ted DiBiase’s “fake” Undertaker in Chicago, IL.
– On April 7, 1995 in Pikeville, KY, The Undertaker and Tracey Smothers beat The Gangstas and D-Lo Brown in a “handicap loser salutes the flag” match.
– The Undertaker defeated Mabel in a “casket” match at In Your House #5.
– At Wrestlemania XII, The Undertaker beat Diesel (Kevin Nash).
– The Undertaker defeated Mankind in a “buried alive” match on October 20, 1996 in Indianapolis, IN.
– In 1997, The Undertaker won Slammies for Best Tattoo and Entrance Music and Star of the Highest Magnitude.
– At Wrestlemania XIII in Rosemont, IL, The Undertaker defeated Sycho Sid for the WWF title.
– At the 1997 Canadian Stampede, The Undertaker pinned the mammoth Vader.
– On October 10, 1997, The Undertaker pinned Hakushi in Tokyo, Japan.
– At Unforgiven ’98, The Undertaker defeated Kane in an “inferno” match in Greensboro, NC.
– The Undertaker defeated Mankind at the 1998 King of the Ring in a “hell in a cell match.” During the match, The Undertaker threw Mankind off the top of the cage, crashing him through the Spanish Announcer’s table.
– The Undertaker won the WWF World Tag Team title with Steve Austin at the 1998 Fully Loaded in Fresno, CA.
– At Wrestlemania XV, The Undertaker defeated the Big Boss Man in a “hell in the cell” match in Philadelphia, PA.
– The Undertaker-Mankind match was voted 1998’s “Match of the Year” by Pro Wrestling Illustrated.
– The Undertaker defeated The Rock at the 1999 King of the Ring.
– At Summerslam ’99 in Minneapolis, MN, The Undertaker and the Big Show defeated Kane and X-Pac for the WWF World Tag Team title.
– On the September 9, 1999 episode of “Smackdown,” the Big Show and The Undertaker relieved The Rock and Mankind of the WWF World Tag Team title in a “buried alive” match.
– Shortly after, the WWF learned that the Undertaker had a groin injury that would keep him out of action for an extended period.
– In February 2000, Calloway suffered a torn pectoral muscle, which required surgery.
– The Undertaker debuted his biker gimmick at Judgment Day ’00 in Louisville, KY and did a run in during the 60 minute Iron Man match between the Rock and Triple H.
– On July 21, 2000, Calloway took a bride (Sara).
– The Undertaker pinned Kurt Angle at Fully Loaded 2000.
– On October 12, 2000, The Undertaker had gallbladder surgery.
– At Armageddon ’00, The Undertaker tossed Rikishi off the “hell in the cell” cage.
– On the December 18, 2000 edition of “Raw,” The Undertaker and The Rock captured the WWF World Tag Team title from Edge and Christian in Greenville, SC.
– In January 2001, The Undertaker and Kane reunited once again.
– At Wrestlemania XVII in Houston, TX, The Undertaker pinned Triple H.
– At the April 17, 2001 “Smackdown” taping in Nashville, TN, The Undertaker and Kane defeated Edge and Christian in a NO-DQ match to win the WWF World Tag Team title.
– The Undertaker defeated Triple H and Austin in a handicap match in the main event at Insurrextion in London, England.
– At the August 7, 2001 “Smackdown” taping in LA, CA, The Undertaker and Kane defeated Chuck Palumbo and Sean O’Haire to capture the WCW World Tag Team title.
– At Summerslam ’01, Undertaker and Kane defeated Diamond Dallas Page and Kanyon for the WWF World Tag Team title in San Jose, CA.
– The Undertaker and Kane successfully defended the WCW World Tag Team title against Kronic at Unforgiven in Pittsburgh, PA.
– At No Mercy ’01, The Undertaker defeated Booker T.
– On the November 26, 2001 edition of “Raw,” The Undertaker turned heel and forced Jim Ross to kiss Mr. McMahon’s posterior.
– At the Vengeance PPV in San Diego, CA, The Undertaker defeated Rob Van Dam to capture the WWF Hardcore title.
– At Wrestlemania X-8, The Undertaker defeated Ric Flair in a no disqualification match. The win was The Undertaker’s tenth straight in the Wrestlemania series.
– The Undertaker was selected #1 by Flair in the WWF brand extension draft for “Raw.”
– At Backlash ’02, The Undertaker defeated Austin to become the #1 contender for the WWF title. Flair served as the special guest referee.
– At Judgment Day ’02 in Nashville, TN, The Undertaker defeated Hulk Hogan for the WWE title.
– The Undertaker successfully defended the WWE title at the 2002 King of the Ring against Triple H.
– On the July 1, 2002 edition of “Raw,” The Undertaker successfully defended the WWE title against Jeff Hardy in a ladder match.
– At Summerslam ’02, Undertaker defeated Test.
– The Undertaker forced the Big Show to submit at the 2003 No Way Out in Montreal.
– At Wrestlemania XIX in Seattle, WA, The Undertaker and Nathan Jones defeated A-Train and the Big Show.
– At Vengeance ’03 in Denver, CO, The Undertaker defeated John Cena.
– The Undertaker defeated A-Train at Summerslam 2003.
– After being “buried alive,” the Undertaker returned with Paul Bearer at Wrestlemania XX and defeated Kane.
– At Judgment Day ’04, The Undertaker defeated Booker T.
– The Undertaker defeated Paul Heyman’s Dudley Boyz in a “concrete crypt” match. After the match, it appeared The Undertaker would save his long time manager, but finished burying him in cement telling Bearer to “rest in peace.”
– At Survivor Series ’04, The Undertaker defeated John Heidenreich.
– At the 2005 Royal Rumble, The Undertaker again defeated Heidenreich, this time in a “casket” match.
– At No Way Out ’05, The Undertaker defeated Luther Reigns.
– The Undertaker defeated Randy Orton at Wrestlemania 21 to improve his undefeated Wrestlemania record to 13-0.
– At the 2005 Great American Bash ’05, The Undertaker defeated Hassan to become the #1 contender to the World Heavyweight title.
– The Undertaker defeated Randy Orton at the 2005 Armageddon in Providence, RI in his seventh “hell in a cell” match.
– At Wrestlemania 22, The Undertaker defeated Mark Henry in a “casket” match to improve his all-time Wrestlemania record to 14-0.
– At the Great American Bash ’06, The Undertaker defeated The Big Show (scheduled to be against The Great Khali) in a “Punjabi Prison” match.
– The Undertaker defeated Mr. Kennedy in a “last ride” match at Armageddon ’06.
– The Undertaker won the 2007 Royal Rumble (entering the match at #30) by eliminating Shawn Michaels in San Antonio, TX.
– At Wrestlemania 23 in Detroit, MI, The Undertaker defeated Batista to capture the World Heavyweight title. The win also improved The Undertaker’s Wrestlemania record to a perfect 15-0.
– On August 1, 2007, The Undertaker was voted into the GERWECK.NET Hall of Fame.
– At Unforgiven ’07, The Undertaker defeated Mark Henry.
– Undertaker defeated Batista, Big Daddy V, MVP, The Great Khali, and Finlay in an elimination chamber match to earn a world title match at Wrestlemania XXIV.
– At Wrestlemania XXIV in Orlando, FL, Undertaker defeated Edge to capture the World Heavyweight title. The win extended Undertaker’s Wrestlemania winning streak to 16-0.
– At Backlash ’08, The Undertaker defeated Edge to retain the World Heavyweight title.
– At Summerslam ’08, The Undertaker defeated Edge in a “hell in a cell” match.
– The Undertaker defeated The Big Show at Cyber Sunday ’08 in a “Last Man Standing” match.
– At the 2008 Survivor Series, The Undertaker defeated The Big Show in a “casket” match.
– The Undertaker defeated Shawn Michaels at Wrestlemania 25 to improve his Mania record to a perfect 17-0.
– At Hell in a Cell in Montreal, Undertaker defeated CM Punk in Montreal to capture the World Heavyweight title in a “Hell in a Cell” match.
– At Bragging Rights ’09, The Undertaker defeated Batista, Rey Mysterio and CM Punk to retain the World Heavyweight title.
– At Survivor Series ’09, The Undertaker defeated The Big Show and Chris Jericho.
– The Undertaker defeated Batista at TLC in a “Chairs” match to remain World Heavyweight title.
– The Undertaker defeated Rey Mysterio to retain the World Heavyweight title at the 2010 Royal Rumble.
– At Wrestlemania 26, Undertaker defeated Shawn Michaels in a “career v. streak” match to improve his Wrestlemania record to 18-0.
– At Wrestlemania 27, Undertaker defeated Triple H in a “No Holds Barred” match to improve the Wrestlemania streak to 19-0.
– The Undertaker defeated Triple H in a “Hell in a Cell” match at Wrestlemania 28 to keep his Mania record perfect at 20-0.
– At Wrestlemania 29, The Undertaker ran his Wrestlemania streak to 21-0 by pinning CM Punk.
– At WrestleMania XXX, The Undertaker lost his undefeated streak after a defeat by Brock Lesnar.